US2023113686A1PendingUtilityA1

Anaerobically curable compositions

Assignee: HENKEL AG & CO KGAAPriority: Apr 1, 2020Filed: Oct 3, 2022Published: Apr 13, 2023
Est. expiryApr 1, 2040(~13.7 yrs left)· nominal 20-yr term from priority
C09J 175/16C08L 33/08C08F 20/18C09J 175/04C08L 75/04C09J 175/14C08F 290/147C08F 283/08C09J 7/30C09J 133/08C08G 18/7621C09K 2003/1065C08F 4/34C08F 290/064C08L 75/16C08F 290/067C08G 18/48C08G 18/672C09J 133/10C08L 33/10
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Claims

Abstract

An anaerobically curable composition comprising:a liquid anaerobically curable component;a solid anaerobically curable component;a solid thermoplastic polyurethane resin having a molecular weight in the range of from 40,000 g/mol to 100,000 g/mol and a melting point in the range of from 40° C. to 80° C.;anda curing component for curing the anaerobically curable components.Advantageously, the compositions of the invention are substantially solid and may be used as threadlockers.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . An anaerobically curable composition comprising:
 a liquid anaerobically curable component;   a solid anaerobically curable component;   a solid thermoplastic polyurethane resin having a molecular weight in the range of from 40,000 g/mol to 100,000 g/mol and a melting point in the range of from 40° C. to 80° C.; and   a curing component for curing the anaerobically curable components.   
     
     
         2 . The composition of  claim 1 , wherein the liquid anaerobically curable component is present in an amount of from about 4 wt % to about 44 wt % based on the total weight of the composition. 
     
     
         3 . The composition of  claim 1 , wherein the solid anaerobically curable component is present in an amount of from about 5 wt % to about 45 wt % based on the total weight of the composition. 
     
     
         4 . The composition of  claim 1 , wherein the solid thermoplastic polyurethane resin is present in an amount of from about 20 wt % to about 75 wt % based on the total weight of the composition. 
     
     
         5 . The composition of  claim 1 , wherein the curing component for curing the anaerobically curable components is present in an amount of from about 0.1 to about 10 wt % based on the total weight of the curable composition. 
     
     
         6 . The composition of  claim 1 , wherein the liquid anaerobically curable component comprises a liquid (meth)acrylate monomer component. 
     
     
         7 . The composition of  claim 6 , wherein the liquid (meth)acrylate monomer component is one or more selected from those having the formula:
   H 2 C=CGCO 2 R 8 ,   wherein G is hydrogen, halogen or alkyl groups having from 1 to 4 carbon atoms, and R 8  is selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, alkaryl or aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted as the case may be with silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, sulfone and the like.   
     
     
         8 . The composition of  claim 1  wherein the solid anaerobically curable component comprises one or more solid (meth)acrylate monomer components. 
     
     
         9 . The composition of  claim 1  wherein the curing component comprises one or more selected from the group consisting of 1-acetyl-2-phenylhydrazine, N,N-dimethyl para toluidine, N,N-diethyl para toluidine, N,N-diethanol para toluidine, N,N-dimethyl ortho toluidine, N,N-dimethyl meta toluidine, indoline, 2-methylindoline, isoindoline, indole, 1,2,3,4-tetrahydroquinoline, 3-methyl-1,2,3,4-tetrahydro-quinoline, 2-methyl-1,2,3,4-tetrahydroquinoline, and 1,2,3,4-tetrahydroquinoline-4-carboxylic acid. 
     
     
         10 . The composition according to  claim 1 , further comprising an initiator of free radical polymerization. 
     
     
         11 . The composition according to  claim 10 , wherein the initiator of free radical polymerization is one or more selected from the group consisting of: cumene hydroperoxide (“CHP”), para-menthane hydroperoxide, t-butyl hydroperoxide (“TBH”), t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butyl cumyl peroxide, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, t-amyl hydroperoxide, 1,2,3,4-tetramethylbutyl hydroperoxide and combinations thereof. 
     
     
         12 . The composition according to  claim 10 , wherein the initiator of free radical polymerisation comprises an encapsulated peroxide. 
     
     
         13 . The composition according to  claim 1 , further comprising a cure accelerator. 
     
     
         14 . The composition according to  claim 13 , wherein the cure accelerator comprises one or more metallocenes; and/or
 a cure accelerator embraced by   
       
         
           
           
               
               
           
         
       
       wherein X is CH 2 , O, S, NR 4 , CR 5 R 6  or C═O; R is one or more of hydrogen, alkyl, alkenyl, alkynl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynl; R 1 -R 6  are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R 7  is hydrogen or CHR 8 R 9 , wherein R 8  and R 9  are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; and n is 0 or 1. 
     
     
         15 . The composition according to  claim 1  provided in tape form, filament form or in the form of a coated substrate. 
     
     
         16 . The composition according to  claim 1  provided as a coating on a thread or a fibre. 
     
     
         17 . A tape comprising an anaerobically curable composition according to  claim 1  and one or more release liners. 
     
     
         18 . A threaded member comprising at least one threaded face, wherein said at least one threaded face comprises an anaerobically curable composition according to  claim 1 . 
     
     
         19 . The threaded member according to  claim 18 , wherein the anaerobically curable composition is in tape form, filament form or in the form of a coated substrate. 
     
     
         20 . The threaded member according to  claim 19 , wherein the anaerobically curable composition in tape form, filament form or in the form of a coated substrate is applied to the threaded face. 
     
     
         21 . A method of manufacturing a threaded member comprising a threadlocking composition, comprising:
 (a) providing at least one threaded member comprising at least one threaded face,   (b) applying to said at least one threaded face, an anaerobically curable composition according to  claim 1 .   
     
     
         22 . The method of manufacturing a threaded member according to  claim 21 , wherein the anaerobically curable composition is in tape form, filament form or in the form of a coated substrate. 
     
     
         23 . The method of manufacturing a threaded member according to  claim 21 , wherein the anaerobically curable composition in tape form, filament form or in the form of a coated substrate is wrapped at least partially around the at least one threaded face of the threaded member. 
     
     
         24 . A method of assembling threaded members comprising:
 (a) providing a first threaded member, comprising at least one threaded face;   (b) applying an anaerobically curable composition according to  claim 1  to said at least one threaded face;   (c) providing a second threaded member capable of matingly engaging said first threaded member;   
       matingly engaging said first and second threaded members and thereby exposing said anaerobically curable composition to an anaerobic environment for a time sufficient for said anaerobically curable composition to cure between said first and second threaded members. 
     
     
         25 . The method according to  claim 24 , wherein the anaerobically curable composition is in tape form, filament form or in the form of a coated substrate. 
     
     
         26 . The method according to  claim 25 , wherein the anaerobically curable composition in tape form, filament form or in the form of a coated substrate is wrapped at least partially around said at least one threaded face. 
     
     
         27 . A method for manufacturing a tape for threadlocking comprising:
 (a) mixing at least one solid thermoplastic polyurethane resin having a molecular weight in the range of from 40,000 g/mol to 100,000 g/mol and a melting point in the range of from 40° C. to 80° C., and solvent;   (b) mixing therewith: a liquid anaerobically curable component, a solid anaerobically curable component and a curing component for curing the anaerobically curable components;   (c) applying the mixture of step (ii) to a release liner;   (d) allowing the solvent to evaporate, to thereby form a tape comprising the anaerobically curable composition according to  claim 1  and a release liner.

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